Kalaheo Hillside Real Estate

Welcome to Kalaheo Hillside, a hidden gem nestled in the heart of Kailua, Oahu. This enchanting neighborhood boasts panoramic views of the lush Ko’olau Mountains and the sparkling turquoise waters of the Pacific Ocean, making it a picturesque paradise for residents and visitors alike. With its serene atmosphere and friendly community, Kalaheo Hillside offers an idyllic retreat from the hustle and bustle of city life.

The charm of Kalaheo Hillside lies not only in its stunning natural beauty but also in its vibrant local culture. The area is known for its spacious lots, well-maintained homes, and lush landscaping, providing a perfect backdrop for families and individuals seeking a tranquil living environment. The neighborhood is also a stone’s throw away from Kailua's pristine beaches, where you can enjoy sunbathing, swimming, or engaging in various water sports.

For those who appreciate outdoor activities, Kalaheo Hillside is surrounded by numerous parks and hiking trails, inviting residents to explore the enchanting landscapes of Oahu. The nearby Lanikai and Kailua Beaches, consistently ranked among the best in the world, are perfect for a day of relaxation or adventure.

In addition to its natural beauty, Kalaheo Hillside is conveniently located near Kailua’s charming town center, where you can find a delightful mix of local shops, cafes, and restaurants. Enjoy fresh farm-to-table dining, unique boutiques, and a welcoming community that embodies the spirit of Aloha.

Whether you’re looking to settle down or simply enjoy a slice of paradise, Kalaheo Hillside is the perfect place to call home. Experience the best of island living in this captivating neighborhood today!

Newest Listings in Kalaheo Hillside

$1,690,000

4 Beds ⋅ 3 Baths ⋅ 202614340 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 DOM

Experience elevated island living in this fully remodeled, single-level home in the heart of Kailua. Renovated from top to bottom, this property feels virtually new and offers the perfect blend of modern design and everyday comfort. The home features a 3-bedroom, 2-bath main residence plus a connected 1-bedroom, 1-bath suite with a kitchenette, providing exceptional flexibility for extended family, guests, a home office, or potential rental income. Inside, a bright open-concept floor plan seamlessly connects the kitchen, living, and dining areas, creating an inviting space for both entertaining and daily living. The bedrooms feature premium DuChâteau hardwood flooring, adding warmth and an elegant finish throughout. A thoughtfully designed hidden laundry room enhances functionality while maintaining clean lines and a spacious feel. Outside, enjoy a fully fenced, oversized backyard—perfect for entertaining, pets, or relaxing in your own private retreat—along with a generous front yard that enhances the home's curb appeal. Turnkey and move-in ready, this exceptional property offers modern island living in one of Oahu's most desirable beach communities.

1225 Mokapu Boulevard, Kailua

$1,590,000

3 Beds ⋅ 2 Baths ⋅ 202614057 MLS ⋅ FS - Fee Simple Tenure ⋅ 9 DOM

Welcome home to this spacious three-bedroom, two-bathroom residence in the highly sought-after Kalaheo Hillside. Freshly painted along with other upgrades throughout, this Kailua home offers a seamless blend of modern comfort and island charm. The open-concept interior is designed for indoor-outdoor living, leading you towards the large, flat fully-enclosed backyard oasis framed by lush tropical landscaping—a perfect backdrop for weekend gatherings or quiet afternoons in the sun. Situated just a short walk Castles Beach and the convenience of Aikahi Shopping Center, this location puts everything Kailua has to offer at your fingertips. Located within the Aikahi school district and just minutes to the vibrant dining and boutique shopping of Kailua town, this property captures the relaxed, active lifestyle you’ve been looking for.

923 Mokapu Boulevard, Kailua

$2,300,000

4 Beds ⋅ 3 Baths ⋅ 202611972 MLS ⋅ FS - Fee Simple Tenure ⋅ 37 DOM

Tucked onto one of Kalaheo Hillside's most sought-after streets, 445 Iliwahi Loop is a fully reimagined 4-bed, 3-bath retreat blending timeless island architecture with a clean, considered renovation — vaulted ceilings, an open great room flowing to covered lanais, and walls of glass framing the pool, gardens and fountains. This generous lot sits against the conservation hillside adding to the peace and quiet of this location. The chef's kitchen pairs a Viking range and Sub-Zero refrigeration w/a generous island open to the dining & living areas. Two primary suites suit multigenerational living or a guest wing, the spa-inspired primary bath w/a soaking tub and oversized shower. Two additional bedrooms w/shared bath PLUS 2 office/flex rooms Outside is your own resort: a sparkling pool (plus spa hookup), mature landscaping, a garden gazebo and covered lanai seating for golden-hour gatherings. NEM metering, 2 Tesla Powerwalls, + a new GACO roof! Freshly painted inside & out, new flooring, lighting & fans throughout. Minutes to Kailua Beach, a short hop to Marine Corps Base Hawaii, and moments from H-3, Pali and Likelike — with Aikahi Shopping Center and dining close at hand.

445 Iliwahi Loop, Kailua

$1,875,000

202610580 MLS ⋅ FS - Fee Simple Tenure ⋅ 62 DOM

Nestled within one of Kailua’s favorite neighborhoods, Kalaheo Hillside, 315 Iliaina Street is filled with potential and island charm. The property includes two separate structures --- a cute, detached cottage studio with a full bath and kitchenette, plus a classic home offering 3 bedrooms, 2 full baths, a great open floor plan, and a separate dining area with large windows looking out to the backyard. Much of the home remains in its original condition, including beautiful koa kitchen cabinet doors that could shine again with restoration. The spacious yard features a large in-ground pool and plenty of room to reimagine the outdoor spaces! Split ACs in each room. Owned PV panels with net metering. Just minutes from Aikahi Shopping Center, Aikahi Elementary School, Kailua’s beaches, shopping, dining opportunities, markets, and so much more! Also close to MCBH Kaneohe, H-3, and Likelike Highway access, this property combines location, flexibility, and opportunity in one of Kailua’s most convenient neighborhoods. (Also listed as MLS#202609716)

315 Iliaina Street, Kailua

$1,875,000

3 Beds ⋅ 3 Baths ⋅ 202609716 MLS ⋅ FS - Fee Simple Tenure ⋅ 62 DOM

Nestled within one of Kailua’s favorite neighborhoods, Kalaheo Hillside, 315 Iliaina Street is filled with potential and island charm. The property includes two separate structures --- a cute, detached cottage studio with a full bath and kitchenette, plus a classic home offering 3 bedrooms, 2 full baths, a great open floor plan, and a separate dining area with large windows looking out to the backyard. Much of the home remains in its original condition, including beautiful koa kitchen cabinet doors that could shine again with restoration. The spacious yard features a large in-ground pool and plenty of room to reimagine the outdoor spaces! Just minutes from Aikahi Shopping Center, Aikahi Elementary School, Kailua’s beaches, shopping, dining opportunities, markets, and so much more! Also close to MCBH Kaneohe, H-3, and Likelike Highway access, this property combines location, flexibility, and opportunity in one of Kailua’s most convenient neighborhoods. Split ACs in each room. PV panels on net metering.

315 Iliaina Street, Kailua

$3,880,000

3 Beds ⋅ 3 Baths ⋅ 202605289 MLS ⋅ FS - Fee Simple Tenure ⋅ 134 DOM

Your dream waterfront Kailua residence. This hidden jewel fronting Kawainui Canal with access to the ocean offers an exceptional blend of contemporary design and Kama‘aina elegance. Architecturally designed and tastefully refreshed, this 3 bdrm, 2.5 ba residence with 3,291 sq ft of living space offers vaulted ceilings (which elevate the sense of space and natural light), fresh interior/exterior paint, vinyl plank flooring, new carpet, and an open chef’s kitchen featuring custom cabinetry, quartz countertops, and a spacious 10’ island. An expansive primary suite overlooks the pool deck with canal and majestic Ko’olau Mountain views. Designed for effortless indoor/outdoor living, there are multiple lanais along with a swimming pool—ideal for entertaining and everyday relaxation. Lush landscaping on the 14,866 sq ft lot enhances the already tranquil setting. The cul-de-sac location maximizes the already private location. An owned photovoltaic system with a net metering agreement adds energy efficiency. Just minutes from Kailua’s beaches, shopping, and dining, this home offers elevated island living in one of Oahu’s most desirable neighborhoods.

1110 Ilikala Place, Kailua

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.